The most interesting part of Spike Jonze’s latest film Her, is not the introspective main character, Theodore Twombly (played deftly by Joaquin Phoenix), nor is it Scarlett Johansson’s sultry-voiced computerized companion, in fact the thing that sticks out to me most is not a character at all. It’s a pair of pants. From the moment the trailer for Her hit the internet a handful of months ago, there was already talk of Phoenix’s startling high-waisted trousers, but I don’t think that anyone was ready for the sheer volume of near-nipple high pants in the film. Just about every publication from Esquire, to Entertainment Weekly, to The Guardian, to the damn Today Show, has covered costume designer Casey Storm’s decision to clothe the film’s male ensemble in pants that hit well above the navel.

Earlier this fall, Alfonso Cuaron’s space epic Gravity landed on movie screens worldwide, propelling the audience into the final frontier with one of the most renowned cinematic experiences of the past decade. While Gravity, in my opinion, lives up to the hype and then some, it is impossible to watch any sort of intergalactic movie and not think of Stanley Kubrick’s 1967 film 2001: A Space Odyssey. While Gravity from frame one is about the unending solitude of space, 2001 is more concerned with the complexities of space exploration, making it as visually stunning as Gravity, but for different reasons. Gravity’s strength lies in its 3-D shots and extended sequences capturing the incomparable vastness of outer space, while 2001 presents space as more of a futuristic playground, complete with these immense colorful sets and modernist costumes designed by none other than Hardy Amies.

In the late sixties Amies was at the top of his game, guiding his unique eponymous label to become both a traditional Savile Row powerhouse, and a forward thinking fashion brand. It was these two minds that made Amies perfect for the role of costume designer on Kubrick’s film, as 2001 presented both the refined corporate side of space exploration, as well as the more visionary angle of astronauts floating in unchartered territory. Amies essentially developed two separate collections for this film – one of Anglo-fied office ready outfits, and one of avant-garde cosmic costumes.

By now, Whit Stillman has achieved a unique cultural status, at once iconic and elusive. His films have such a specific, literate sensibility that devotees hoard favorite lines like beloved family recipes (‘I don’t think Ted is a fascist of the marrying kind,’ remains very dear). And though he’s oft-quoted, Stillman has been a stranger for too long—he’s been executing his own Maneuver X, Barcelona partisans might say. After a dozen years, he’s back. Damsels in Distress, his university picture starring Greta Gerwig, opens in New York and LA today.

We spoke this week in a Madison Avenue hotel suite where Bloomberg News, of all things, was on the television in the background.

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David Coggins: Is that Alexander Olch in the first shot of Damsels in Distress?

Whit Stillman: It is, and he also repeats, at the end, when they talk about cool people. His very recognizable silhouette goes through twice, kind of bad continuity. He’s wearing a suit and sneakers. I think you should talk to him about shoes.

DC: I will. It’s funny you mention coolness though, because in all your films there’s a distinction between people who understand what’s going on and those who are struggling to figure it out, and a lot of analysis about that fine line.

WS: I agree with the Violet character [in Damsels in Distress] in that debate, that if you really want to be cool, you have to tamp down your humanity a little bit. You’ve got to de-emote, depersonalize. But I tried to be fair to Lily’s character, and what she says does make sense, that yes, we need normal people so things work right.

For instance, I find dealing with Sony Pictures, I’m not so good with the deadlines, because I want it to be really right, but they need to get it by a certain time, so there’s a bit of a drama when ‘Whit needs to approve something.’ It’s been good, but I feel that the practical people get things done. And often I find there’s a conflict between a certain kind of particularism, and getting-it-done-ism. I don’t like to say perfectionism, because nothing is perfect, but if you want to get things in a particular way, that goes against getting it done on time.

Part at home dentistry instructional film and part Alone in the Wilderness, Dead River Rough Cut is a documentary about a couple of leathery guys living a backwoods existence away from the bothers of social interaction and the convenience (read: health standards) of modern life. The DVD was part of my ACL Twitter gift guide, but I thought it was worth expanding on a little for those that might have missed it.

The film documents a secluded and cracker barrel life in the Maine woods. Its an astonishing look at a different way of life. Dead River Rough Cut also has the honor of being the number one requested film at the Maine State Penitentiary — you can’t even make this shit up. Worth a look if you are into toothless roughnecks that spend their whole day hunting, slaughtering pigs and riding around on primitive snowmobiles. You can purchase the DVD here.

The Road To… series is comprised of seven films starring Bing Crosby, Bob Hope and Dorothy Lamour that were released between 1940 and 1962. If you watch Family Guy, you are most likely familiar with the song in the above video and the overall concept. Co-stars Bing and Bob are up there (in my mind at least) with the best ever silver screen pairings. My favorite of the series is Road to Utopia, which takes place in Alaska. For the uninitiated, Netflix has them all available to rent. Get to queuing.

Visually, Paris, Texas could be the most American movie ever. I don’t even think the Texas tourism board could make the state look any better than these filmmakers did. Funny thing is, the picture was made by a bunch of Europeans. I suppose people get a better perspective of something when they are on the outside looking in. What’s amazing about this 1984 film is the enduring nature of the style — especially with what is happening in the world today. Worth a watch for inspiration alone. Some of my favorite looks below. [Paris, Texas at the Criterion Collection]

News of the launch of the Wolverine 1000 Mile collection first came in February of 2009. It was around that time that I met some of the people from Wolverine and wrote about the collection. Later, Wolverine invited me to a little event they put together in the city and I got a chance to meet all of the people involved in the 1000 Mile line — all good people. After that we started talking more and eventually Wolverine hired my public relations firm to help out with the 1000 Mile Collection — which has been a lot of fun. (In case you missed it, that was my full disclosure.)

A project that we have been working on over the past several months is the special edition, limited-quantity Wolverine 1000 Mile boot with the imprint 721LTD. The undertaking, which is named for the original 1000 Mile boot reference number, was pulled directly from the company’s archives from over 125 years of boot making. To celebrate the provenance of the 721LTD boots, Wolverine commissioned a film series (directed by my friend Sean Sullivan) to document the journey of these unique 1000 Mile boots. The opening chapter takes you on a pilgrimage to Chicago to visit the Horween leather company, America’s finest tannery and supplier of shell cordovan to the 721LTD 1000 Mile boots.

I’m proud and excited to share this short film with you and to take you inside Horween, a truly special place and national treasure. These kinds of projects are what it is all about for me. To work with good people like the folks at Wolverine, Sullivan and all of the people at Horween on something as legitimate as the 1000 Mile boots.